(Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol

Base Information

• Chemical Name: (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol
• CAS No.: 600714-96-3
• Molecular Formula: C₅₈H₈₈O₆Si₃
• Molecular Weight: 965.59

Synonyms:(Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol

Chemical Property of (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol

There total 18 articles about (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol (600714-96-3)

Guidance literature:

Multi-step reaction with 18 steps

1: 91 percent / diethyl ether / -78 °C

2: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

3: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

4: Dibal-H / CH₂Cl₂ / -78 °C

5: NaBH₄ / methanol / 0 °C

6: pyridine / 25 °C

7: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

8: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

9: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

10: diethyl ether / -78 °C

11: 93 percent / imidazole / CH₂Cl₂

12: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

13: diethyl ether / -78 °C

14: 85 percent / 2,6-lutidine / -78 °C

15: OsO₄; NMO; NaIO₄ / acetone; H₂O

16: 78 percent / diethyl ether / -78 °C

17: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

18: Dibal-H / toluene / -80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; 9: Swern oxidation / 17: Swern oxidation;

DOI:10.1021/ol034958l

Reference yield:

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (106357-24-8) → (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol (600714-96-3)

Guidance literature:

Multi-step reaction with 17 steps

1: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

2: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

3: Dibal-H / CH₂Cl₂ / -78 °C

4: NaBH₄ / methanol / 0 °C

5: pyridine / 25 °C

6: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

7: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

8: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

9: diethyl ether / -78 °C

10: 93 percent / imidazole / CH₂Cl₂

11: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

12: diethyl ether / -78 °C

13: 85 percent / 2,6-lutidine / -78 °C

14: OsO₄; NMO; NaIO₄ / acetone; H₂O

15: 78 percent / diethyl ether / -78 °C

16: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

17: Dibal-H / toluene / -80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; 8: Swern oxidation / 16: Swern oxidation;

DOI:10.1021/ol034958l

Reference yield:

(1S,2S)-1-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2-methylbut-3-enyl prop-2-enoate (468738-71-8) → (Z)-(3S,4R,5R,6S,8S,11S,12S,13S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,14-bis-(tert-butyl-diphenyl-silanyloxy)-12-methoxymethoxy-3,5,11,13-tetramethyl-tetradeca-1,9-dien-4-ol (600714-96-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

2: Dibal-H / CH₂Cl₂ / -78 °C

3: NaBH₄ / methanol / 0 °C

4: pyridine / 25 °C

5: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

6: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

7: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8: diethyl ether / -78 °C

9: 93 percent / imidazole / CH₂Cl₂

10: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

11: diethyl ether / -78 °C

12: 85 percent / 2,6-lutidine / -78 °C

13: OsO₄; NMO; NaIO₄ / acetone; H₂O

14: 78 percent / diethyl ether / -78 °C

15: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

16: Dibal-H / toluene / -80 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; 7: Swern oxidation / 15: Swern oxidation;

DOI:10.1021/ol034958l

upstream raw materials:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-5-methyl-5,6-dihydro-2H-pyran-2-one

(1S,2S)-1-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2-methylbut-3-enyl prop-2-enoate

Downstream raw materials:

C₆₄H₁₀₂O₆Si₄

(Z)-(2R,3S,4S,5S,7S,10S,11S,12S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7,13-bis-(tert-butyl-diphenyl-silanyloxy)-11-methoxymethoxy-2,4,10,12-tetramethyl-tridec-8-enoic acid methyl ester

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